PIMP MY MOLECULE! AGLYCON (Logo) (Header Picture)

A simple access to the D-mannosidase inhibitor 1-deoxymannojirimycin

Josef Spreitz, Arnold E. St├╝tz and Tanja M. Wrodnigg

Abstract:
Crystalline 1,3,4,5-tetra-O-acetyl-6-bromo-6-deoxy-keto-d-fructose was prepared by reaction of 1,3,4,5-tetra-O-acetyl-d-fructopyranose with triphenylphosphane dibromide in dichloromethane. Subsequent deprotection followed by reaction of the free 6-bromodeoxyfructofuranose with sodium azide in N,N-dimethylformamide furnished the corresponding 6-azidodeoxyketose. Catalytic hydrogenation led to 1-deoxymannojirimycin in 27% overall yield from 1,3,4,5-tetra-O-acetyl-d-fructopyranose. This access is simple, inexpensive, high-yielding and clearly suitable for multigram preparations.